2-((6-(((1R,3s,5S)-8-(cyclopropylsulfonyl)-8-azabicyclo[3.2.1]octan-3-yl)oxy)-5-methylpyrimidin-4-yl)amino)-5-fluorobenzonitrile | 1147552-88-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 2-((6-(((1R,3s,5S)-8-(cyclopropylsulfonyl)-8-azabicyclo[3.2.1]octan-3-yl)oxy)-5-methylpyrimidin-4-yl)amino)-5-fluorobenzonitrile
• CAS: 1147552-88-2
• 化学式: C₂₂H₂₄FN₅O₃S
• 分子量: 457.529
• InChiKey: SQAOFWPVTLZDNS-BCDXTJNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  108.21
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  tert-butyl (1S,5R)-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate 在 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 生成 2-((6-(((1R,3s,5S)-8-(cyclopropylsulfonyl)-8-azabicyclo[3.2.1]octan-3-yl)oxy)-5-methylpyrimidin-4-yl)amino)-5-fluorobenzonitrile
  参考文献：
  名称：

  Discovery of a nortropanol derivative as a potent and orally active GPR119 agonist for type 2 diabetes

  摘要：

  The lead optimization studies of a series of GPR119 agonists incorporating a nortropanol scaffold are described. Extensive structure-activity relationship (SAR) studies of the lead compound 20f led to the identification of compound 36j as a potent, single digit nanomolar GPR119 agonist with high agonist activity. Compound 36j was orally active in lowering blood glucose levels in a mouse oral glucose tolerance test and increased plasma insulin levels in a rat hyperglycemic model. It showed good to excellent pharmacokinetic properties in rats and monkeys and no untoward activities in counter-screen assays. Compound 36j demonstrated an attractive in vitro and in vivo profile for further development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.035